Out of Sync
When people are actually able to buy a Palm Pre, it isn’t going to play well with iTunes. Not consistently for any length of time (months or years), anyway.
Palm can show a demo in which their phone seems to work great with iTunes. But you can do anything in a demo. For example, in a demo Adobe can show Flash running on an iPhone, and that’s not going to happen either.
All Apple has to do to stop this — which they have every reason to want to do — is:
1. Sue Palm to make them stop, possibly basing the action on DMCA — i.e. the only way you can make a non-Apple device work with iTunes is by hacking a private communications protocol that you agreed not to hack when you bought the Apple device and when you started running iTunes on your computer.
2. If Apple doesn’t win a lawsuit against Palm, then they can simply start modifying the communications protocol between iTunes and iPods/iPhones. They can do this an unlimited number of times, because they can issue software updates to the iPods/iPhones, and thus make any arbitrary changes to the protocol. In other words, they don’t have to rely on imperfections in Palm’s simulation of being an Apple device, which Palm can eventually clean up completely. Palm can, of course, simulate an older version of the iPod software, but as iTunes marches on, it may eventually refuse to support older protocols. And, you can bet that many new features of iTunes won’t work unless you upgrade the software on your iPod.
If Apple does this, could Palm then sue Apple for anti-competitive practices, as Microsoft was sued for changing Windows in ways that arbitrarily harmed some third-party products? Roger McNamee, a major player at Palm, already seems to be hinting that they will, when he says that Apple is “practically a monopolist.”
But such a suit won’t win. Microsoft invited everyone everywhere to write apps for Windows, and published APIs and development systems for them to do exactly that. Apple has done no such thing with the iTunes-to-iPod communications protocol. If Apple doesn’t want to support a slew of third-party products when making fixes, updates, and other changes to their systems, and went as far as trying to legally force those third-parties to stop hacking those systems, then is Apple really likely to lose a suit charging them with the crime of modifying their own, private, unpublished protocols to the detriment of those same third-parties?

Update 2009.07.19 — Apple not only broke the Pre’s hacked iTunes syncing ability a few days ago, they issued the following statement about it:
[The iTunes 8.2.1 update] disables devices falsely pretending to be iPods, including the Palm Pre. As we’ve said before, newer versions of iTunes may no longer provide syncing functionality with unsupported digital media players.
In other words: We blocked the Pre, we blocked it on purpose, and we’re publicly saying so. This isn’t underhanded sabotage of the competition, it’s intentional prevention of piggybacking that we never invited anyone to perform.
